Chapter
I Production and Bioactivity of Oligosaccharides
I.I Naturally Occurring Oligosaccharides
1 Bioactivity of Human Milk Oligosaccharides
1.2 Structural uniqueness of human milk oligosaccharides
1.2.1 Lewis blood group and secretor-specific components in milk
1.2.2 Total human milk oligosaccharides content and concentrations of single components
1.3 Human milk oligosaccharides and their functions in the gastrointestinal tract
1.3.1 Human milk oligosaccharides and gut microbiota
1.3.2 Human milk oligosaccharides and antiadhesion effects
1.3.3 Human milk oligosaccharides and effects on epithelial cells and immune modulation
1.4 Human milk oligosaccharides and systemic effects
1.5 Human milk oligosaccharides and studies in animals and humans
1.6 Conclusion and perspective
2 Production and Bioactivity of Bovine Milk Oligosaccharides
2.2 Bovine milk oligosaccharides’ composition
2.2.1 Colostrum versus mature milk bovine milk oligosaccharides composition
2.2.2 Comparison with human milk oligosaccharides’ composition
2.3 Bovine milk oligosaccharides concentration
2.4 Resistance to digestion
2.5 Oligosaccharides biological activities
2.5.1 Bifidogenic activity
2.5.2 Pathogen prevention
3 Production and Bioactivity of Oligosaccharides in Plant Foods
3.2 Chemical structure and natural occurrence of oligosaccharides in plant foods
3.2.1 Fructan type oligosaccharides
3.2.2 -Galactooligosaccharides
3.3 Production of naturally occurring plant oligosaccharides
3.4 Scientific evidence on the bioefficacy of plant oligosaccharides and mechanisms of action
3.4.1 Studies of plant oligosaccharides on gut microbiota
3.4.2 Studies of plant oligosaccharides on immune system
3.4.3 Studies of plant oligosaccharides on mineral absorption
3.4.4 Studies of plant oligosaccharides and lipid metabolism
3.4.5 Studies of plant oligosaccharides and glucose homeostasis
3.4.6 Studies of plant oligosaccharides and regulation of food intake, fat mass and body weight
3.4.7 Study of plant oligosaccharides on oxidative stress
3.5 Conclusions and future perspectives
4 Production and Bioactivity of Oligosaccharides from Chicory Roots
4.1 Production of oligosaccharides from chicory roots
4.1.1 Dynamics of inulin biosynthesis and biodegradation in the chicory root
4.1.1.2 Biosynthesis of inulin in the chicory root
4.1.1.3 Biodegradation of inulin in the chicory root
4.1.1.4 Resulting composition of chicory root
4.1.1.5 Analytical methodology
4.1.2 Industrial production of inulin from chicory roots
4.1.2.1 Agricultural aspects
4.1.2.2 Industrial inulin processing
4.2 Bioactivity of oligosaccharides from chicory roots
4.2.1 Basic physiology and nutritional aspects
4.2.2.2 The prebiotic effect
4.2.2.3 Paediatric applications
4.2.2.4 Energy intake and healthy weight management
4.2.2.5 Mineral bio-availability
5 Production and Bioactivity of Pectic Oligosaccharides from Fruit and Vegetable Biomass
5.1 Production of pectic oligosaccharides
5.1.1 Extraction of pectic oligosaccharides
5.1.3 Separation and purification methods for oligosaccharides
5.2 Bioactivity of pectic oligosaccharides
5.2.1 Prebiotic properties
5.2.4 Heavy metals excretion
5.2.5 Antiadhesion of pathogens
6 Production and Bioactivity of Oligosaccharides from Biomass Hemicelluloses
6.1 Hemicelluloses: general aspects
6.2 Manufacture of oligosaccharides from hemicellulosic polymers
6.2.1 Manufacture and purification of xylooligosaccharides
6.2.2 Manufacture and purification of mannooligosaccharides
6.2.3 Manufacture and refining of other hemicellulose-derived saccharides
6.2.3.1 Xyloglucan-derived oligosaccharides
6.2.3.2 Arabinogalactan-derived oligosaccharides
6.2.3.3 Mixed linkage b-glucans derived oligosaccharides
6.3 Properties of hemicellulose-derived oligosaccharides
6.3.1 Properties of xylooligosaccharides
6.3.2 Properties of mannooligosaccharides
6.3.3 Properties of products obtained by hydrolysis of other hemicellulosicsaccharides
7 Starch Hydrolysis Products with Physiological Activity in Humans
7.2 Starch degradation may yield minor saccharides with physiological activity
7.2.4 Minor oligosaccharides
7.3 Physiological activity of starch hydrolysis products
7.3.4 Isomaltooligosaccharides (IMO)
8 Biosynthesis and Bioactivity of Exopolysaccharides Produced by Probiotic Bacteria
8.1 Bacterial exopolysaccharides
8.2 Biosynthesis of exopolysaccharides in Lactobacillus and Bifidobacterium
8.3 Production and purification of exopolysaccharides
8.4 Bioactivity of exopolysaccharides from probiotics
8.4.1 Exopolysaccharides as modulators of the immune system
8.4.2 Exopolysaccharides as modulators of the intestinal microbiota
8.4.3 Other beneficial actions
8.5 Concluding remark and future trends
I.II Non-Naturally Occurring Oligosaccharides
9 Production and Bioactivity of Oligosaccharides Derived from Lactose
9.2 Mono- and disaccharides
9.2.1.1 Chemical isomerization
9.2.1.2 Enzymatic synthesis
9.2.2.1 Isomerization of lactose
9.2.2.2 Transgalactosylation of lactose
9.2.2.3 Uses of lactulose
9.3.1 Enzymatic transfructosylation of lactose
9.3.2 Enzymatic transgalactosylation of sucrose
9.3.3 Uses of lactosucrose
9.4 Galactooligosaccharides
9.4.1 Enzymatic synthesis from lactose
9.4.2 Enzymatic synthesis from lactulose
9.4.3 Chemical isomerization of galactooligosaccharides
9.4.4 Assessment of beneficial effects of oligosaccharides derived from lactose and lactulose
9.4.5 Uses of galactooligosaccharides
9.5 Other oligosaccharides
9.6 Purification of carbohydrates derived from lactose
10 Production and Bioactivity of Glucooligosaccharides and Glucosides Synthesized using Glucansucrases
10.1 Glucooligosaccharides from lactic acid bacteria
10.2 Glucan and glucooligosaccharides synthesis by glucansucrases
10.2.1 Glucan synthesis by glucansucrase
10.2.2 Glucansucrases genes, alternation of glucansucrase, and its oligosaccharide synthesis by the acceptor reaction
10.3 Production of glucooligosaccharides
10.4 Bioactivities of glucan and glucooligosaccharides
10.4.1 Glucooligosaccharides as prebiotics
10.4.2 Bowel function improvement
10.4.3 Anticariogenic properties
10.4.4 Stimulation of immunity
10.5 (Oligo)glucosides synthesized by glucansucrases and their functionalities
11 Production and Bioactivity of Fructan-Type Oligosaccharides
11.2.1 The transfructosylation reaction
11.2.2 Structural and biochemical differences between fructosyltransferases from GH32 and GH68 families
11.2.3 Microbial enzymes involved in the biosynthesis of fructan-type oligosaccharides
11.2.3.3 Other fructosyltransferases
11.2.4 Plant enzymes involved in the biosynthesis of fructan-type oligosaccharides
11.2.4.1 Monocots versus dicots
11.3 Functional properties of fructan-type oligosaccharides
11.3.1.1 Prevention of infection with bacterial pathogens
11.3.1.3 Mineral absorption
11.3.1.4 Defense functions
11.3.1.5 Systemic effects
11.3.3 Application of fructooligosaccharides as food ingredients
12 Application of Immobilized Enzymes for the Synthesis of Bioactive Fructooligosaccharides
12.1 Enzyme immobilization
12.1.1 Classification of immobilization methods
12.1.2 Selection of the immobilization method
12.2 Immobilized biocatalysts for the production of fructooligosaccharides
12.3 Production of fructooligosaccharides with a covalently immobilized fructosyltransferase
12.4 Production of fructooligosaccharides with alginate-entrapped fructosyltransferases
12.4.1 Entrapment of fructosyltransferase from Aspergillus aculeatus
12.4.2 Entrapment of levansucrase from Zymomonas mobilis
12.5 Conclusions and future trends
I.III Assessment of Bioactivity
13 In Vitro Assessment of the Bioactivity of Food Oligosaccharides
13.3 Interaction with the host
13.4 Invitro fermentation models of the gut to study bioactivity of oligosaccharides
13.4.1 Single stage reactors or semi-continuous systems
13.4.2 Multi-compartmental continuous systems
13.5 Applications of invitro fermentation models to study the effect of oligosaccharides on the gut microbiome
13.6 Mechanistic studies using 13C-labeled oligosaccharides and fibers
13.6.1 Incorporation of stable isotopes in biomass
13.6.2 Metabolite production – use of stable isotopes
13.6.3 Use of 6’-sialyl lactose, a human milk oligosaccharide, by the gut microbiota
13.6.4 The microbiota is linked with obesity, through energy extraction from dietary components in the form of short-chain fatty acids
13.7 Invitro cell culture systems
14 In Vivo Assessment of the Bioactivity of Food Oligosaccharides
14.1 The prebiotic concept
14.2 In vivo assessment of dietary oligosaccharides as prebiotics
14.2.1 Resistance to digestion of dietary oligosaccharides
14.2.2 In vivo fermentation of dietary oligosaccharides by intestinal microbiota
14.2.3 Modulatory effect of food oligosaccharides in gut microbiota
15 Fractionation of Food Bioactive Oligosaccharides
15.2.1 Ultrafiltration (UF)
15.2.2 Nanofiltration (NF)
15.2.3 Combined membrane processing
15.3 Chromatographic techniques
15.3.1 Size-exclusion chromatography (SEC)
15.3.3 Simulated moving-bed chromatography
15.3.4 Activated charcoal
15.3.5 Other chromatographic techniques
15.4 Fractionation techniques using solvents
15.4.1 Selective solvent solubility
15.4.3 Supercritical fluid extraction (SFE)
15.4.4 Pressurized liquid extraction (PLE)
15.4.5 Microwave-assisted extraction (MWAE)
15.5 Microbiological and enzymatic treatments
16 Classical Methods for Food Carbohydrate Analysis
16.2 Sample preparation and purification
16.3 Classical methods for total sugar analysis
16.3.1 Total sugar analysis for carbohydrate
16.3.1.1 Phenol–sulfuric acid assay
16.3.1.2 Anthrone-sulfuric acid methods
16.3.1.3 Uronic acid determination
16.3.2 Measurement of total reducing sugar
16.3.2.1 Somogyi–Nelson method
16.3.2.2 Other methods for reducing sugar analysis
16.4 Classical methods for monosaccharide determination
16.4.1 Sample preparation
16.4.2.1 Enzymatic method for monosaccharide analysis
16.4.2.2 Enzymatic methods for oligosaccharides analysis
16.4.3 Anion-exchange chromatography
16.4.4 Gas liquid chromatography
16.5 Classical methods for structure characterization of polysaccharides
16.5.1 Partial acid hydrolysis
16.5.3 Methylation analysis
16.6 Some physical methods for carbohydrate analysis
16.6.2 Specific gravity (hydrometers)
16.7 Classical methods for dietary fiber analysis
16.7.2.1 Uppsala method (AOAC 994.13; AACC 32-25)
16.7.2.2 Enzymaticgravimetric methods (AACC 32-50.01)
17 Infrared Spectroscopic Analysis of Food Carbohydrates
17.2.1 Mid-infrared spectra of monosaccharides in aqueous solutions
17.2.2 Mid-infrared spectroscopic analysis of interaction between monosaccharides and water
17.2.3 Analysis of interaction between saccharides and other components
17.3.1 Mid-infrared spectroscopic analysis of disaccharides in aqueous solutions
17.3.1.1 Mid-infrared spectra of disaccharides in aqueous solutions
17.3.1.2 Mid-infrared spectroscopic analysis of interaction between disaccharides and water
17.3.2 Mid-infrared spectroscopic analysis of maltooligosaccharides in aqueous solutions
17.3.3 Application of mid-infrared spectroscopy for polysaccharides
17.4.1.1 Quantitative analysis of monosaccharides and disaccharides in juices
17.4.1.2 Estimation of the polymerization degree of maltooligosaccharides by mid-infrared spectroscopy
17.4.2 For actual process – application of yogurt fermentation
18 Structural Analysis of Carbohydrates by Nuclear Magnetic Resonance Spectroscopy and Molecular Simulations: Application to Human Milk Oligosaccharides
18.1.1 Probiotics and prebiotics
18.1.2 Structures of human milk oligosaccharides
18.2 Nuclear Magnetic Resonance spectroscopy
18.2.1 Nuclear spin-relaxation
18.2.1.1 13C auto-relaxation
18.2.1.2 1H,1H nuclear Overhauser effects
18.2.2 1H,13C and 13C,13C scalar spin-spin coupling constants
18.2.3 1H and 13C residual dipolar couplings
18.2.3.1 Theoretical background
18.2.3.2 Molecular interpretation
18.2.3.3 Experimental considerations
18.3 Molecular dynamics computer simulations
18.4 Three-dimensional structures of human milk oligosaccharides
18.4.1 Lacto-N-neotetraose
18.4.2 Lacto-N-fucopentaose 1
18.4.3 Lacto-N-fucopentaose 2
19 Analysis of Food Bioactive Oligosaccharides by Thin-Layer Chromatography
19.2 Thin-layer chromatography
19.3 Thin-layer chromatography analysis of food bioactive oligosaccharides
19.3.1 Sample preparation
19.3.2 Chromatographic system (Stationary and mobile phases)
19.3.2.1 Thin-layer chromatography and high-performance thin-layer chromatography silica gel layers
19.3.2.2 Amino-bonded silica gel thin-layers
19.3.2.3 Cellulose thin-layers
19.3.3 Detection (visualization) and quantification of oligosaccharides
19.3.3.1 Chemical detection reagents
19.3.3.2 Quantification of oligosaccharides
19.3.4 Coupling thin-layer chromatography-mass spectrometry
19.3.5 Thin-layer chromatography-flame ionization detection
20 Gas Chromatographic Analysis of Food Bioactive Oligosaccharides
20.2.1 Sample pretreatment
20.2.2 Chemical treatments
20.2.2.1 Direct analysis of derivatized oligosaccharides
20.2.2.2 Analysis of oligosaccharide monomers
20.3.1 The chromatographic flow and the mobile phase
20.3.2.1 Splitsplitless (SS) injector
20.3.2.2 On-column injector and programmed temperature injectors
20.3.3.2 Stationary phase
20.3.4.1 Gas chromatography-flame ionization detector
20.3.4.2 Gas chromatography-mass spectrometry
20.4 Advanced analysis by comprehensive two-dimensional gas chromatography (GC×GC)
21 Analysis of Bioactive Food-Sourced Oligosaccharides by High-Performance Liquid Chromatography
21.2 Derivatization of oligosaccharides
21.3 High-performance liquid chromatography analysis of bioactive food sourced oligosaccharides
21.3.1 High pH anion exchange chromatography
21.3.2 Reversed-phase chromatography
21.3.3 Hydrophilic interaction chromatography
21.3.4 Chromatography on graphitized carbon
21.4 Application of high-performance liquid chromatography for the separation of bioactive food sourced oligosaccharides
21.4.1 Human and bovine milk oligosaccharides
21.4.2 Nonmilk oligosaccharides
21.5 Novel analytical methods
22 Capillary Electrophoresis and Related Techniques for the Analysis of Bioactive Oligosaccharides
22.2 Capillary electrophoresis analysis of functional oligosaccharides
22.2.1 Analysis of oligosaccharides in food, plants, algae, bacteria, and fungi
22.2.2 Analysis of milk-derived oligosaccharides
22.3 Capillary electrophoresis analysis of glycosaminoglycan-derived oligosaccharides
22.3.1 Analysis of oligosaccharides derived from hyaluronan
22.3.2 Analysis of sulfated GAGs
22.3.3 Chip-based CE for the analysis of GAG-derived oligosaccharides
22.4 Capillary electrophoresis analysis of oligosaccharides derived from glycoproteins
22.4.1 Analysis of N-linked glycans
22.4.2 Analysis of O-linked glycans
23 Mass Spectrometric Analysis of Food Bioactive Oligosaccharides
23.2 Instrumentation for mass spectrometric analysis of oligosaccharides
23.2.2 Mass spectrometry analyzers in oligosaccharide studies
23.3 Fragmentation techniques, processes and nomenclature
23.4 Applications to analysis of food bioactive oligosaccharides
23.4.1 Neutral oligosaccharides
23.4.2 Acidic oligosaccharides
23.4.2.1 Sialylated oligosaccharides
23.4.2.2 Sulfated oligosaccharides
23.4.2.3 Glucuronic and galacturonic acid oligosaccharides
23.4.2.5 N- and O-linked glycans
23.5 Strategies, challenges, and conclusion
III Prebiotics in Food Formulation
24 Nutritional and Technological Benefits of Inulin-Type Oligosaccharides
24.2 Nutritional aspects of chicory inulin and oligofructose
24.3 Technical properties of chicory inulin and oligofructose
24.3.2 Inulin and gel formation
24.3.3 Texturizing properties and fat replacement
24.3.5 Process stability of fructans
24.4 Technical functionality in food applications
24.4.1 “Sugar out, fiber in”
24.4.2.3 Other food categories
24.4.3 General fiber concepts
25 Industrial Applications of Galactooligosaccharides
25.2 Global market development for galactooligosaccharides
25.3 Nutritional benefits of galactooligosaccharides for infants and young children
25.3.1 Gut microbiota in breastfed and bottle-fed infants
25.3.2.1 Pathogens, toxins and infections
25.3.2.2 Immunomodulation
25.3.3 Calcium absorption
25.3.4 Stool consistency and frequency
25.4 Legislative aspects and safety of galactooligosaccharides
25.4.2 Infant nutrition applications
25.4.2.1 European regulation
25.4.2.3 Australia and New Zealand
25.4.3.1 European Union legislation
25.4.4 Safety aspects of galactooligosaccharides
25.4.4.2 Galactooligosaccharides
25.5 Galactooligosaccharide products
25.5.1 Characterization of galactooligosaccharides products
25.5.2 Physico-chemical properties of galactooligosaccharides
25.5.3 Physiological properties of galactooligosaccharides
25.5.3.2 Glycemic index (GI)
25.6 Applications of galactooligosaccharides
25.6.1 Application of galactooligosaccharides in infant nutrition
25.6.2 Application of galactooligosaccharides in medical nutrition
25.6.3 Application of galactooligosaccharides in dairy products and beverages
25.7 Stability of galactooligosaccharides
25.8 Concluding remarks and future developments
26 Successful Product Launch: Combining Industrial Technologies with Adapted Health Ingredients
26.1 Developing new foods: the health dimension
26.2 A global approach to successful food conception, applied to the case of digestive health
26.2.1 Simple and efficient: the food-concept sheet
26.2.1.1 The need to improve diets nutritionally: the case of malnutrition
26.2.1.2 How? The markers of good health
26.2.1.3 When food meets nutrition
26.2.2 The scope of nondigestible oligosaccharides as digestive health ingredients
26.2.3 The health claim regulations compliance: two examples
26.2.4 First soluble oligosaccharide product allowed to bear a health claim in Europe: Galactofructose
26.2.5 Digestive health: whats already on the market
26.3 The ingredients and the formulation: practical aspects of the incorporation of nondigestible oligosaccharides
26.3.1 A practical approach to include nondigestible oligosaccharides
26.3.2 Formulating healthy food: how to integrate ingredients and remain into the food scope
26.3.3 Principal characteristics
26.3.3.1 Polyvalent ingredient for diversified applications
26.3.3.4 Sugar concentration and density – sweetness properties
26.4 Elaborating new food products with nondigestible oligosaccharides
26.4.1 A sensitive application: infant nutrition
26.4.2.2 Drinks – fruit juices and milk drinks
26.4.3 Product developments in Africa
26.4.3.1 Kindirmo, nono and warankasi
26.4.3.3 Fermented beverages
26.5 What are the key success factors? Synthesis and comments from an expert chef
26.5.1 Product development: key success factors and the route to successful product launch
26.5.2 Comments from a chef: Mickael Azouz (World Champion, Member of the “Académie Culinaire de France”)
Epilogue: Concluding Thoughts on Food Bioactive Oligosaccharides
Food Oligosaccharides
：Production, Analysis and Bioactivity
( Institute of Food Technologists Series )
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